DE1667842A1 - Verfahren zum Herstellen von katalytisch wirksamem ss-Titanchlorid und Anwenden fuer die Polymerisation von Diolefinen - Google Patents
Verfahren zum Herstellen von katalytisch wirksamem ss-Titanchlorid und Anwenden fuer die Polymerisation von DiolefinenInfo
- Publication number
- DE1667842A1 DE1667842A1 DE19681667842 DE1667842A DE1667842A1 DE 1667842 A1 DE1667842 A1 DE 1667842A1 DE 19681667842 DE19681667842 DE 19681667842 DE 1667842 A DE1667842 A DE 1667842A DE 1667842 A1 DE1667842 A1 DE 1667842A1
- Authority
- DE
- Germany
- Prior art keywords
- aluminum
- group
- aromatic
- titanium
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229910001040 Beta-titanium Inorganic materials 0.000 title claims description 50
- 238000000034 method Methods 0.000 title claims description 28
- 150000001993 dienes Chemical class 0.000 title claims description 19
- 238000006116 polymerization reaction Methods 0.000 title description 23
- 238000004519 manufacturing process Methods 0.000 title description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 title description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 57
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 52
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 41
- 229910052782 aluminium Inorganic materials 0.000 claims description 40
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 33
- 239000003446 ligand Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 26
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000002723 alicyclic group Chemical group 0.000 claims description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000012721 stereospecific polymerization Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 238000012360 testing method Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 150000001491 aromatic compounds Chemical class 0.000 claims 2
- 241000282326 Felis catus Species 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- -1 Titanium halides Chemical class 0.000 description 37
- 239000003054 catalyst Substances 0.000 description 24
- 229910010038 TiAl Inorganic materials 0.000 description 14
- 239000002904 solvent Substances 0.000 description 12
- 239000010936 titanium Substances 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 9
- 150000002170 ethers Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 150000003568 thioethers Chemical class 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 229910052719 titanium Inorganic materials 0.000 description 6
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000003849 aromatic solvent Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 description 4
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000000536 complexating effect Effects 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 230000007717 exclusion Effects 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229920001195 polyisoprene Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical class CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002370 organoaluminium group Chemical group 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 2
- MTAYDNKNMILFOK-UHFFFAOYSA-K titanium(3+);tribromide Chemical compound Br[Ti](Br)Br MTAYDNKNMILFOK-UHFFFAOYSA-K 0.000 description 2
- HUYLAMJIPCOVOM-UHFFFAOYSA-K triiodotitanium Chemical compound [Ti+3].[I-].[I-].[I-] HUYLAMJIPCOVOM-UHFFFAOYSA-K 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 2
- 230000003313 weakening effect Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- SVJIEGOVQBGOSU-UHFFFAOYSA-N (4-methylphenyl)-propan-2-ylalumane Chemical compound C1(=CC=C(C=C1)[AlH]C(C)C)C SVJIEGOVQBGOSU-UHFFFAOYSA-N 0.000 description 1
- PRPLGWFQYUPYBN-UHFFFAOYSA-N (4-methylphenyl)-propylalumane Chemical compound C1(=CC=C(C=C1)[AlH]CCC)C PRPLGWFQYUPYBN-UHFFFAOYSA-N 0.000 description 1
- HITROERJXNWVOI-SOFGYWHQSA-N (5e)-octa-1,5-diene Chemical compound CC\C=C\CCC=C HITROERJXNWVOI-SOFGYWHQSA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- 150000000093 1,3-dioxanes Chemical class 0.000 description 1
- 150000000094 1,4-dioxanes Chemical class 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- NBABFNIOSUDVLM-UHFFFAOYSA-N 1-(2-methylpropylsulfanyl)naphthalene Chemical compound C1=CC=C2C(SCC(C)C)=CC=CC2=C1 NBABFNIOSUDVLM-UHFFFAOYSA-N 0.000 description 1
- HTXWHKJWSFNHKM-UHFFFAOYSA-N 1-butylsulfanylnaphthalene Chemical compound C1=CC=C2C(SCCCC)=CC=CC2=C1 HTXWHKJWSFNHKM-UHFFFAOYSA-N 0.000 description 1
- DVPVENXICBSLEW-UHFFFAOYSA-N 1-cyclohexylsulfanylnaphthalene Chemical compound C1CCCCC1SC1=CC=CC2=CC=CC=C12 DVPVENXICBSLEW-UHFFFAOYSA-N 0.000 description 1
- NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 description 1
- KSADSZUNUVNDEC-UHFFFAOYSA-N 1-ethylsulfanylnaphthalene Chemical compound C1=CC=C2C(SCC)=CC=CC2=C1 KSADSZUNUVNDEC-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- DYKYMRSTKCJTAN-UHFFFAOYSA-N 1-hexylsulfanylnaphthalene Chemical compound C1=CC=C2C(SCCCCCC)=CC=CC2=C1 DYKYMRSTKCJTAN-UHFFFAOYSA-N 0.000 description 1
- DKICYCNWKRHPFR-UHFFFAOYSA-N 1-methylsulfanylnaphthalene Chemical compound C1=CC=C2C(SC)=CC=CC2=C1 DKICYCNWKRHPFR-UHFFFAOYSA-N 0.000 description 1
- QLAWAFBTLLCIIM-UHFFFAOYSA-N 1-naphthalen-1-ylsulfanylnaphthalene Chemical compound C1=CC=C2C(SC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 QLAWAFBTLLCIIM-UHFFFAOYSA-N 0.000 description 1
- TZPCGEVFZZYCIY-UHFFFAOYSA-N 1-octylsulfonyloctane Chemical compound CCCCCCCCS(=O)(=O)CCCCCCCC TZPCGEVFZZYCIY-UHFFFAOYSA-N 0.000 description 1
- MVGLQWLVKVJGBL-UHFFFAOYSA-N 1-pentylsulfanylnaphthalene Chemical compound C1(=CC=CC2=CC=CC=C12)SCCCCC MVGLQWLVKVJGBL-UHFFFAOYSA-N 0.000 description 1
- NREKZWPYGVASKZ-UHFFFAOYSA-N 1-propylsulfanylnaphthalene Chemical compound C1=CC=C2C(SCCC)=CC=CC2=C1 NREKZWPYGVASKZ-UHFFFAOYSA-N 0.000 description 1
- LFEXGBPVZBXATF-UHFFFAOYSA-N 2,3-dimethylbenzenesulfonamide Chemical compound CC1=CC=CC(S(N)(=O)=O)=C1C LFEXGBPVZBXATF-UHFFFAOYSA-N 0.000 description 1
- JRCZSHDOYYZKAW-UHFFFAOYSA-N 2-(4-methylphenyl)ethylalumane Chemical compound C1(=CC=C(C=C1)CC[AlH2])C JRCZSHDOYYZKAW-UHFFFAOYSA-N 0.000 description 1
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
- UQRLAGGSKUVKMJ-UHFFFAOYSA-N 2-methylpropylsulfanylbenzene Chemical compound CC(C)CSC1=CC=CC=C1 UQRLAGGSKUVKMJ-UHFFFAOYSA-N 0.000 description 1
- GNOMLLKHNCKJRX-UHFFFAOYSA-N 2-phenylethylalumane Chemical compound C1(=CC=CC=C1)CC[AlH2] GNOMLLKHNCKJRX-UHFFFAOYSA-N 0.000 description 1
- DTADFKNTXRGGOR-UHFFFAOYSA-N 3-methylbutylsulfanylbenzene Chemical compound CC(C)CCSC1=CC=CC=C1 DTADFKNTXRGGOR-UHFFFAOYSA-N 0.000 description 1
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- BJEDPZTUMCKCTD-UHFFFAOYSA-N 3-phenylpropylalumane Chemical compound C(C1=CC=CC=C1)CC[AlH2] BJEDPZTUMCKCTD-UHFFFAOYSA-N 0.000 description 1
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
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- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 241000746181 Therates Species 0.000 description 1
- 229910010068 TiCl2 Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- VJWWWWAWJYNGOU-UHFFFAOYSA-N anisole tripropylalumane Chemical compound C1(=CC=CC=C1)OC.C(CC)[Al](CCC)CCC VJWWWWAWJYNGOU-UHFFFAOYSA-N 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- LBKYCOGBBDATCR-UHFFFAOYSA-N benzyl(diethyl)alumane Chemical compound CC[Al](CC)CC1=CC=CC=C1 LBKYCOGBBDATCR-UHFFFAOYSA-N 0.000 description 1
- AIWXNWDZGADCFW-UHFFFAOYSA-N benzyl(propan-2-yl)alumane Chemical compound C(C1=CC=CC=C1)[AlH]C(C)C AIWXNWDZGADCFW-UHFFFAOYSA-N 0.000 description 1
- YGHMTLQLIZMTLJ-UHFFFAOYSA-N benzyl(propyl)alumane Chemical compound C(C1=CC=CC=C1)[AlH]CCC YGHMTLQLIZMTLJ-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- LLHTVHHWJJDSSP-UHFFFAOYSA-N bis(4-methylphenyl)alumane Chemical compound C1(=CC=C(C=C1)[AlH]C1=CC=C(C=C1)C)C LLHTVHHWJJDSSP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- DKRDVQXZJNVXDP-UHFFFAOYSA-M bromo(dibutyl)alumane Chemical compound [Br-].CCCC[Al+]CCCC DKRDVQXZJNVXDP-UHFFFAOYSA-M 0.000 description 1
- SVOZEWXYCOBNAY-UHFFFAOYSA-M bromo(dioctyl)alumane Chemical compound [Br-].CCCCCCCC[Al+]CCCCCCCC SVOZEWXYCOBNAY-UHFFFAOYSA-M 0.000 description 1
- JKFJJYOIWGFQGI-UHFFFAOYSA-M bromo-bis(2-methylpropyl)alumane Chemical compound [Br-].CC(C)C[Al+]CC(C)C JKFJJYOIWGFQGI-UHFFFAOYSA-M 0.000 description 1
- YKLUJQMOFAXHHI-UHFFFAOYSA-N butan-2-ylsulfanylbenzene Chemical compound CCC(C)SC1=CC=CC=C1 YKLUJQMOFAXHHI-UHFFFAOYSA-N 0.000 description 1
- YCURFOQQPNHZAO-UHFFFAOYSA-N butyl naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OCCCC)=CC=CC2=C1 YCURFOQQPNHZAO-UHFFFAOYSA-N 0.000 description 1
- JETFNRIIPBNRAT-UHFFFAOYSA-N butylsulfanylbenzene Chemical compound CCCCSC1=CC=CC=C1 JETFNRIIPBNRAT-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000002091 cationic group Chemical class 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- DFGSACBYSGUJDZ-UHFFFAOYSA-M chloro(dihexyl)alumane Chemical compound [Cl-].CCCCCC[Al+]CCCCCC DFGSACBYSGUJDZ-UHFFFAOYSA-M 0.000 description 1
- ISFMCQATCMRFPY-UHFFFAOYSA-M chloro(diphenyl)alumane Chemical compound [Cl-].C=1C=CC=CC=1[Al+]C1=CC=CC=C1 ISFMCQATCMRFPY-UHFFFAOYSA-M 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- LWSWHXZQBIFYLZ-UHFFFAOYSA-N cyclohexylsulfanylbenzene Chemical compound C1CCCCC1SC1=CC=CC=C1 LWSWHXZQBIFYLZ-UHFFFAOYSA-N 0.000 description 1
- 150000001940 cyclopentanes Chemical class 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- OTACYDLCOLOKPA-UHFFFAOYSA-N dibenzyl(ethyl)alumane Chemical compound C=1C=CC=CC=1C[Al](CC)CC1=CC=CC=C1 OTACYDLCOLOKPA-UHFFFAOYSA-N 0.000 description 1
- DODCHQVKECHKRP-UHFFFAOYSA-N dibenzylalumane Chemical compound C(C1=CC=CC=C1)[AlH]CC1=CC=CC=C1 DODCHQVKECHKRP-UHFFFAOYSA-N 0.000 description 1
- FLJCSPOMUZKFCO-UHFFFAOYSA-M dibutyl(iodo)alumane Chemical compound [I-].CCCC[Al+]CCCC FLJCSPOMUZKFCO-UHFFFAOYSA-M 0.000 description 1
- VJRUISVXILMZSL-UHFFFAOYSA-M dibutylalumanylium;chloride Chemical compound CCCC[Al](Cl)CCCC VJRUISVXILMZSL-UHFFFAOYSA-M 0.000 description 1
- VTZJFPSWNQFPCQ-UHFFFAOYSA-N dibutylaluminum Chemical compound CCCC[Al]CCCC VTZJFPSWNQFPCQ-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- MVGUIMCFFQICHB-UHFFFAOYSA-N diethyl(phenyl)alumane Chemical compound CC[Al](CC)C1=CC=CC=C1 MVGUIMCFFQICHB-UHFFFAOYSA-N 0.000 description 1
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 1
- PPQUYYAZSOKTQD-UHFFFAOYSA-M diethylalumanylium;iodide Chemical compound CC[Al](I)CC PPQUYYAZSOKTQD-UHFFFAOYSA-M 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylphenylamine Natural products CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 239000012897 dilution medium Substances 0.000 description 1
- QRQUTSPLBBZERR-UHFFFAOYSA-M dioctylalumanylium;chloride Chemical compound CCCCCCCC[Al](Cl)CCCCCCCC QRQUTSPLBBZERR-UHFFFAOYSA-M 0.000 description 1
- ZUGPRXZCSHTXTE-UHFFFAOYSA-N diphenyl sulfate Chemical compound C=1C=CC=CC=1OS(=O)(=O)OC1=CC=CC=C1 ZUGPRXZCSHTXTE-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- HIVRDDZUKVNKAO-UHFFFAOYSA-N diphenylalumane Chemical compound C1(=CC=CC=C1)[AlH]C1=CC=CC=C1 HIVRDDZUKVNKAO-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical class CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- ZMXPNWBFRPIZFV-UHFFFAOYSA-M dipropylalumanylium;chloride Chemical compound [Cl-].CCC[Al+]CCC ZMXPNWBFRPIZFV-UHFFFAOYSA-M 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- GJJASJCGLOUWAC-UHFFFAOYSA-N ethoxycyclohexane Chemical compound CCOC1CCCCC1 GJJASJCGLOUWAC-UHFFFAOYSA-N 0.000 description 1
- SMCMEVQBOQDRPJ-UHFFFAOYSA-N ethyl(diphenyl)alumane Chemical compound C=1C=CC=CC=1[Al](CC)C1=CC=CC=C1 SMCMEVQBOQDRPJ-UHFFFAOYSA-N 0.000 description 1
- NEPIVOURWZEXGS-UHFFFAOYSA-N ethyl-bis(4-methylphenyl)alumane Chemical compound C=1C=C(C)C=CC=1[Al](CC)C1=CC=C(C)C=C1 NEPIVOURWZEXGS-UHFFFAOYSA-N 0.000 description 1
- AEHWKBXBXYNPCX-UHFFFAOYSA-N ethylsulfanylbenzene Chemical compound CCSC1=CC=CC=C1 AEHWKBXBXYNPCX-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 description 1
- DOHLZBMKORLTKE-UHFFFAOYSA-N hexylsulfanylbenzene Chemical compound CCCCCCSC1=CC=CC=C1 DOHLZBMKORLTKE-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- TUAINSCBEUWUOI-UHFFFAOYSA-M iodo(dipropyl)alumane Chemical compound [I-].CCC[Al+]CCC TUAINSCBEUWUOI-UHFFFAOYSA-M 0.000 description 1
- MBZZFFPUTBWWTG-UHFFFAOYSA-M iodo-bis(2-methylpropyl)alumane Chemical compound [I-].CC(C)C[Al+]CC(C)C MBZZFFPUTBWWTG-UHFFFAOYSA-M 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- FGGAOQTXQHKQOW-UHFFFAOYSA-N n,n-diphenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 FGGAOQTXQHKQOW-UHFFFAOYSA-N 0.000 description 1
- VRUKENOGLFMZNY-UHFFFAOYSA-N n-cyclohexyl-n-phenylaniline Chemical compound C1CCCCC1N(C=1C=CC=CC=1)C1=CC=CC=C1 VRUKENOGLFMZNY-UHFFFAOYSA-N 0.000 description 1
- ZMGSLAFYHVDQDX-UHFFFAOYSA-N n-methyl-n-naphthalen-1-ylnaphthalen-1-amine Chemical compound C1=CC=C2C(N(C=3C4=CC=CC=C4C=CC=3)C)=CC=CC2=C1 ZMGSLAFYHVDQDX-UHFFFAOYSA-N 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
- BCFKYKHGGFAUAF-UHFFFAOYSA-N n-phenyl-n-propylaniline Chemical compound C=1C=CC=CC=1N(CCC)C1=CC=CC=C1 BCFKYKHGGFAUAF-UHFFFAOYSA-N 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- DUGRRXREOWMDFE-UHFFFAOYSA-N pentylsulfanylbenzene Chemical compound CCCCCSC1=CC=CC=C1 DUGRRXREOWMDFE-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- ZKGDHJAHOGRQEP-UHFFFAOYSA-N phenyl(propyl)alumane Chemical compound C1(=CC=CC=C1)[AlH]CCC ZKGDHJAHOGRQEP-UHFFFAOYSA-N 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- VKBFQELXJIPDFJ-UHFFFAOYSA-L propylaluminum(2+);dibromide Chemical compound [Br-].[Br-].CCC[Al+2] VKBFQELXJIPDFJ-UHFFFAOYSA-L 0.000 description 1
- NWYDLOBJQIJDGH-UHFFFAOYSA-N propylsulfanylbenzene Chemical compound CCCSC1=CC=CC=C1 NWYDLOBJQIJDGH-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 229920000576 tactic polymer Polymers 0.000 description 1
- VEUCZKAZCRSEMP-UHFFFAOYSA-N tert-butylsulfanylbenzene Chemical compound CC(C)(C)SC1=CC=CC=C1 VEUCZKAZCRSEMP-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- MCWWHQMTJNSXPX-UHFFFAOYSA-N tribenzylalumane Chemical compound C=1C=CC=CC=1C[Al](CC=1C=CC=CC=1)CC1=CC=CC=C1 MCWWHQMTJNSXPX-UHFFFAOYSA-N 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- JOJQVUCWSDRWJE-UHFFFAOYSA-N tripentylalumane Chemical compound CCCCC[Al](CCCCC)CCCCC JOJQVUCWSDRWJE-UHFFFAOYSA-N 0.000 description 1
- JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 0.000 description 1
- WSITXTIRYQMZHM-UHFFFAOYSA-N tris(4-methylphenyl)alumane Chemical compound C1=CC(C)=CC=C1[Al](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WSITXTIRYQMZHM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62732867A | 1967-03-31 | 1967-03-31 | |
| US64981467A | 1967-06-29 | 1967-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1667842A1 true DE1667842A1 (de) | 1971-06-24 |
Family
ID=27090408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681667842 Pending DE1667842A1 (de) | 1967-03-31 | 1968-03-05 | Verfahren zum Herstellen von katalytisch wirksamem ss-Titanchlorid und Anwenden fuer die Polymerisation von Diolefinen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE712130A (enExample) |
| DE (1) | DE1667842A1 (enExample) |
| FR (1) | FR1568173A (enExample) |
| GB (1) | GB1196354A (enExample) |
| NL (1) | NL6804463A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3366937D1 (en) * | 1982-10-27 | 1986-11-20 | Shell Int Research | Process for the preparation of polyisoprene |
-
1968
- 1968-02-28 GB GB959768A patent/GB1196354A/en not_active Expired
- 1968-03-05 DE DE19681667842 patent/DE1667842A1/de active Pending
- 1968-03-11 FR FR1568173D patent/FR1568173A/fr not_active Expired
- 1968-03-13 BE BE712130D patent/BE712130A/xx unknown
- 1968-03-29 NL NL6804463A patent/NL6804463A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE712130A (enExample) | 1968-07-15 |
| NL6804463A (enExample) | 1968-10-01 |
| GB1196354A (en) | 1970-06-24 |
| FR1568173A (enExample) | 1969-05-23 |
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